Anthracene dye and a process of manufacture



Patented Aug. 17, 1926.

UNITED STATES PATENT OFFICE.

IVAN GUBELMAN N, OF SOUTH MILWAUKEE, WISCONSIN, ASSIGNOR TO THE NEWPORTCUMPANY, OF CARROLLVILLE, WISCONSIN, A CORPORATION 'OF DELAWARE.

ANTHBACENE DYE AND A PROCESS OF MANUFACTURE.

No Drawing. App'1ication filed May 9, 1925. Serial Io. 29,217.

agents such as anhydrous sodium acetate or sodium carbonate andcatalyzers such as basic copper acetate may be used to facilitate thereaction.

The following example will serve to illustrate my invention in apreferred form, but I do not wish to limit the process to this example.7

Example: Suspend 50 parts by weight of dibrom-pyranthrone in 600 partsby weight This invention relates to coloring matters of the anthraceneseries and a process of making the same, more particularly to thecoloring matters obtained by the condensa- 6 tion of a halogenatedpyranthrone body with aminodibenzanthrone.

By amino-dibenzanthrone is meant the coloring'matter obtained from thecaustic alkali fusion of benzanthrone and subse- 10 quent nitration andreduction. This coloring matter dyes cotton from a hydrosultite vat,yielding green shades on mild oxidation and black shades on strongeroxidation. v By pyranthrone is meant the coloring matter obtained byheating 2, 2dimethyl-1, l-dianthraquinonyl. This coloring matter dyescotton from a hydrosulfite vat, yielding orange shades on oxidation. It1s known in the chemical arts as Pyranthrone and shall hereinafter bereferred to by this name.

The condensation reaction between the halogenated pyranthrone body andaminodibenzanthrone results in a coloring matter of the type ofamino-dibenzanthrone, 50 parts by weight of anhydrous sodium acetate inthe form of a fine powder,'and 10 parts by weight of basic copperacetate as catalyzer. Heat the mixture under agitation to 210 C. for aperiod of 20 hours. Cool the reaction mixture to 60 C. and add 400'parts by weight of denatured alcohol. Stir the mixture 1 hour andfilter ofl the dark brown reaction product. Wash the filter cake withdenatured alcohol and hot Water until the solvent and After drying andgrinding, the reaction product constitutes a dark brown to black powder,which, from a hydrosulfite vat, dyes cotton a dull bluish-violet shadewhich oxi- 'dizes to a rich brown shade on exposure to air or othersuitable o'xydi'zing agents.

. .'-R. in which R represents the pyranthrone complex and R theamino-dibenzanthrone, and 3 in the formation of a halogen acid. Thereaction proceeds best in the presence of a high boiling solvent attemperatures rang ing between 150and 210 C. Condensation tweendibrom-pyranthrone and amino-dibenthe following formula The exactposition of the bromine atom remainingin the pyranthrone radicle and ofthe coupling bond is not known. The sec- 70 0nd bromine atom uniteswithone hydrogen atom from the amino group to form hydro bromic acid. 1

above example is 210 0., I have found that by varying the temperatureabove and below 210, varibus shades of brown product are obtained. Thecoloring matters thus obtained give shades on dyeing that are exof drynitrobenzol. Add 40 parts by weight the inorganic salts have beeneliminated.

zanthrone is probably best represented by The product obtained by thereaction be- While the temperature specified in the tremely fast-"cowashing, light and other infiuences. The coloring 'matters themselvesare insoluble in hot and cold water,'. sparingly soluble in dilute acidsand organic solvents, but usually more so inorganic high.

boiling solvents. They dissolve in concentrated sulfuric acid, giving ablue to purple color, and they are precipitated out aga n on dilutionwith water. They are, however,

easily soluble in alkaline hydrosulfitesolution.

I am aware process may be v'ariedthrough a Wide range withoutdepartingfrom the spirit of this invention, and I do not desirelimiting'the patent grantedother than as necessitated by the prior art.

I claim as my invention:

1. The process of producing coloring matters of the anthracene serieswhich consists in heating a halogenated pyran'thronebody withamino-dibenzanthrone in the presence of a-high boilingsolvent and a.neutralizing agent,

' 2. Theprocess of producing coloring matters of the anthracene series,which consists in heating a halogenated pyranthrone body withamino-dibenzanthrone in the presence of a high boiling solvent, aneutralizing agent and copper salts.

said coloring matters being in general dark brown powders, which, from ahydrosulfite vat, dye cotton a violet shade, which shade oxidizes to arich brown shade on exposure to air or other oxidizing agents. i

boiling solvent and a neutralizingagent.

that numerous detailsof the 3. The process of producing coloring mattersof the anthracenef series'; which consists in heating dibrom-pyranthronewith aminodibenzanthrone in the presence of a high 4. The process ofproducingbcoloring matters of the anthracene series y heatingdibrom-pyranthrone with annno-dibenzanthrone in the-presence of a highboiling solvent, anhydrous sodium acetate as a neutral- .40 izing' agentand a catalyzer. 5. As new articles of manufacture, the

coloringmatters of the anthracene series which are obtained by'heating ahalogenated pyranthrone body with amino-dibenzanthrone. 5 l:

, 6. As new articles of manufacture, the coloring matters of theanthracene 'series which are obtained by heating a brominatedpyranthrone body vwith -amino-dibenzan- A throne.

7 The process of producing coloring matters of the anthracene series,which consists in heating a halogenated pyr'anthrone body withamino-dibenzanthrone, 5 8. As a new article of manufacture, color--- ingmatters of the anthracene series having most probably the followinggeneral formula v0 I I -9. As new articles of manufacture, colorlngmatters of the anthracene series having most probably the followingformula:

said coldring matters being in general dark 11. Materials dyed coloringmatters brown powders, which, from a hydrosulfitc described in claim 9.

.Vat, dye cotton a violet shade, which shade In testimony whereof I havehere' Q oxidizes to a rich brown shade on exposure scribed my'name.

5 to airor other oxidizing agents. 10. Materials dyed with coloringmatters IVAN GUTBEIMANN; described in claim 8. I i

